C-2/C-3 Annulation and C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters | Zendy

Barbora Bajtos | Zendy; Ming Yu | Zendy; Hongda Zhao | Zendy; Brian L. Pagenkopf | Zendy

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C-2/C-3 Annulation and C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters

Author(s) -

Barbora Bajtos,

Ming Yu,

Hongda Zhao,

Brian L. Pagenkopf

Publication year - 2007

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja067821+

Subject(s) - annulation , chemistry , stereocenter , indole test , alkylation , cyclopropane , stereochemistry , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis , ring (chemistry)

The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.

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